Acid ortho-hydroxy azo dyestuffs capable of being chromed



UNITED STATES PATENT OFFICE ACID bRTHO-HYDROXY AZO DYESTUFFS CAPABLE OF BEING CHROME!) Karl Zahn and Heinrich Koch, Frankfort-on-the- Main-Hochst, Germany, assignors to General Aniline Works, Inc., New York, N. Y., a corporation of Delaware Nolirawing. Application June 16, 1933, Seri No. 676,205. In Germany June 30, 1932 4 Claims. (01. 260-76) The present invention relates tonew acid orthocatalyst, under superatmospheric pressure in a hydroxy azodyestufis which are capable of being suitable solvent or diluent, such as alcohol or chromed, more particularly it relates to disazo Water, or by hydrogenating a di-acyl compound dyestuffs which are obtainable by coupling one of' 2,2'-dihydroXy-l,l'-dinaphthyl and splitting 5 mol of 2,2-dihydroxy1,1 dinaphthyl-ar octooil the acyl radicals from the hydrogenation prodhydride of the formula: uct by saponification. It has a melting point of CH2 139 C. to 140 C. The manufacture of the said compound is more fully disclosed in our co-pending application Serial No. 676,204 filed June 16, i0 H20 1933 for Hydrogenation products from 2,2-dihydroxyand 2,2'di-O-acyl-1,1-dinaphthy1 in the name of Karl Zahn and Heinrich Koch. The following example serves to illustrate the H2O OH invention, but it is not intended to limit it therelil to, the parts being by weight:

23.4 parts of fi-nitro-Z-aminophenol-4-sulfonic 3 acid are diazotized in 60 parts of water and 1D with 2 mols of a sulfo ortho h droxy-diazo parts of concentrated hydrochloric acid with 7 pound of the benzene o naphthalene series. parts Of sodium nitrite, and the whole iS added The new dyestuffs thus obtained may be repin a Solution of parts of '-d ydro 1'- resentedby the general formula: dinaphthyl-ar-octohydride in 200 parts of water CH and 30 parts of caustic soda solution of 40 B. O H When the coupling is finished, the solution is acid- P ,5 I ified by means of concentrated hydrochloric acid 29 6 0H 011 until it gives an acid reaction to Congo paper.

\ T The dyestuff which has been precipitated is fil- I tered by suction and dried; it forms a brown powder. The dyestufi dyes wool from an acid mg bath. The after-chromed dyeings possess brown 59 H l shades.

2 The dyestufi corresponds to the following for- CH ortho) l 0 on mula.

SOsH wherein the Rs stand for radicals of the benzene "a N=N- W or naphthalene series. H2O

The non-hydrogenated simple and easily 210- g cessible 2,2-dihydroxy-l,l-dinaphthy1 (fi-di- OH H naphthol) is not applicable for the production of azo dyestuffs as it does not couple with diazo CH2 an compounds. HZC/ OH 50311 We have now found that the hydrogenation product from 2,2'-dihydroxy-1,1-dinaphthyl, =N i. e. the ar-octohydro-2,2'-dihydroxy-1,1'-di- 0H2 naphthyl is capable of being coupled with diazo 0 11 N02 45 compounds and yields disazo dyestuffs among By using instead of 6-nitro-2-aminopheno1-4- which those obtainable with sulfo-ortho-hydroxysulfonic acid equivalent quantities of 4-nitro-2- diazo compounds are particularly distinguished aminophenol-G-sulfonic acid, 2-aminophenol-4- by good fastness properties. The chromed dyesulfonic acid, 2-aminophenol-5-sulionic acid, 4- ings on wool possess besides a very good fastness chloro-Z-aminophenol-6sulfonic acid, l-am- 50 to washing, fulling and potting an excellent fastinc-2 -naphthol-4-sulfonic acid, nitro-l-aminoness to light. 2-naphtho1-4su1fonic acid or other sulfo-or The 2,2 dihydroxy 1,1'-dinaphyl ar tho-hydroXy-amino-compounds of the benzene or octohydride is obtainable by treating 2,2'-dihynaphthalene series as diazotizing component, droxy-1,1-dinaphthyl with hydrogen in the presdyestufis are obtained which dye wool similar ence of a hydrogenation catalyst, such as a nickel tints.

The after-chromed dyeings are distinguished by a very good fastness to washing, fulling and potting and an excellent fastness to light.

We claim:

1. The acid ortho-hydroXy-azo dyestufis of the general formula:

wherein the Rs stand for radicals or" the benzene or naphthalene series, which dyestuffs'dye wool from an acid bath and are capable of being afterchronied, the chromed dyeings possessing brown tints or" good fastness properties.

2. The acid ortho-hydroxy-azo dyestuffs of thegeneral formula:

wherein the Xs stand for hydrogen, N02 or halogen, which dyestufis dye wool from an acid bath and are capable of being after-chromed, the chromed dyeings possessing brown tints of good fastness properties.

which dyestufif forms, when dry, a brown powder and yields on wool from an acid bath brown tints which, when after-chromed, possess very good fastness to Washing, fulling and potting and excellent fastness to light.

4. The acid 0rtho-hydr0Xy-azo dyestuffs of the formula;

which dyestuff forms, when dry, a brown powder and yields on wool from an acid bath brown tints which, when after-chromed, possess very good fastness to washing, fulling and potting and excellent fastness to light.

KARL ZAHN. HEINRICH KOCH. 

